I Left My $100K Job to Hack Independently (Here's What Happened) episode artwork

EPISODE · Aug 31, 2026 · 56 MIN

I Left My $100K Job to Hack Independently (Here's What Happened)

from The I.T. Career Podcast · host The Bearded I.T. Dad - Dakota Snow

Unlock your dream job in IT with our proven community:https://itcareerjob.com/Learn how a solo penetration tester builds a successful security firm without a massive corporate team behind him. See the reality of independent cybersecurity consulting.Tyler Ramsbey left the safety of a major penetration testing company to launch his own firm, Kairosec. This conversation breaks down the logistics of operating as a one-person business in an industry dominated by giant agencies. You will see how he manages to compete with multi-million dollar infrastructure companies while working entirely on his own.Whether you are an aspiring ethical hacking career seeker or an established security professional, this breakdown offers a clear look at the path to independence. We cover the specific challenges of solo security auditing and what it actually takes to run a solo operation in the high-stakes world of corporate cybersecurity.Subscribe for weekly cybersecurity breakdowns, and let me know in the comments if you want to see more interviews with independent security experts.🖥️ Sites Mentioned in this episode:LinkedIn: https://www.linkedin.com/in/tyler-ramsbey-86221643/YouTube: https://www.youtube.com/@UC_82czjFMgsYMjodhG_4mIwHack Smarter: https://www.hacksmarter.org/catalogKairo Sec: https://kairos-sec.com/🔗 Don’t wait—click here to start your tech career journey: https://thebeardeditdad.com/itcareeraccelerator/Exclusive Career Resources✅ Weekly Insider Tips: https://thebeardeditdad.ck.page/55f710292b🎧 Listen to The I.T. Career Podcast HERE:➡︎ YT: https://itdad.info/ytpodcast➡︎ Apple: https://itdad.info/apple➡︎ Spotify: https://itdad.info/spotifyTimestamps:00:00 - Solo Ethical Hacker vs Giant Cybersecurity Agency01:05 - How Tyler Ramsbey Built Cyrosc & Hacksmarter03:13 - Boutique Pentesting Firm vs Cheap Penetration Testing06:32 - Why I Left My W2 Pentesting Job to Go Solo11:22 - Balancing Full-Time Job, Family, and YouTube Content Creation15:01 - How Much Money You Need Saved Before Quitting Your Job19:24 - How to Build Personal Brand Authority in Cybersecurity25:11 - First 24 Hours of a Web App Pentest (Step-by-Step)30:20 - Finding Broken Access Control & Username Enumeration Vulnerabilities33:55 - Network Fundamentals First: CCNA vs Network+ for Hackers39:31 - How I Landed My First $10,000 Pentesting Client43:08 - How to Transition From Help Desk to Penetration Tester46:10 - Hacksmarter Training Platform & Hands-On Cyber Labs51:02 - Solo Business Model: Work Less & Make More in CyberDisclaimer: Some of these links are affiliate links where I'll earn a small commission if you make a purchase at no additional cost to you.#pentesting #hacking #cybersecurity

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I Left My $100K Job to Hack Independently (Here's What Happened)

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